We offer services for vacation rental owners who need assistance managing the details of their rental business. From websites, marketing, housekeeping, and emergency services - we can help you rent with confidence and peace of mind. As a property owner, or potential property owner, you’ve obviously fallen in love with the beach, just as we have. Seaside Vacations was founded with the belief that there was a better way to provide outstanding service, implement market leading technology, and provide the very best Eastern Shore Vacation experience possible all while providing value to both our Partners and Guests.

Island Days and Sunny Rays….. Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous Condos sit directly on the Bay with stunning Views of the Bay, Marsh, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or wander down the street to shop and dine in the Historic District. ‘Our Pleasure’- Sunset Bay 306 - offers the Luxury you want, the Amenities you need, and Bay Views that will leave you breathless, all at a family-friendly price! Traveling with a larger group? You can rent Sunset Bay 306 and 307 - right next door! You’ll feel a million miles away from the real world, yet still be close to everywhere you want to be - including Assateague National Seashore, where our famous Wild Ponies roam free! Whether you enjoy searching for Wild Ponies, Beach Combing, Fishing, or just Sunbathing, there’s truly something for everyone in your crew. Our Beaches are wild and wonderful - no highrises, no boardwalks - just beautiful Mother Nature! Did you know that Assateague National Seashore is the most visited National Park in our country? Spend a little time here and you will discover why this is..... As you kick off your Flip Flops in ‘Our Pleasure’s’ spacious Foyer, you’ll be welcomed by Colors of Sand and Sea - muted tones pulled from Nature itself, creating a warm, peaceful, and oh, so welcoming retreat. This Newly Renovated Condo has THE most awesome layout for spending time together, without ever feeling crowded. Relax in the spacious Living Area after a fun-filled day at the Beach, and enjoy Free WiFi, Flat Screen Cable TV with Streaming, and Views that will knock your socks off. With plenty of comfy furnishings, it’s truly a “home away from home”. Stroll out to the Waterfront Balcony and watch Herons, Eagles, and Egrets fish for their morning meal, or enjoy watching children fish a...